4-(3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)morpholine → 4-(3-Chlorophenoxy)-6-(3-morpholin-4-yl-phenyl)-1,2,3,4-tetrahydro-[1,8]naphthyridine

HRID 659462

Reaktionsgleichung

Reaktionsgleichung von HRID 659462
Br[C:2]1[CH:3]=[C:4]2[C:9](=[N:10][CH:11]=1)[NH:8][CH2:7][CH2:6][CH:5]2[O:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[CH:14]=1.CC1(C)C(C)(C)OB([C:28]2[CH:29]=[C:30]([N:34]3[CH2:39][CH2:38][O:37][CH2:36][CH2:35]3)[CH:31]=[CH:32][CH:33]=2)O1>C(OCC)(=O)C.CCCCCC>[Cl:19][C:15]1[CH:14]=[C:13]([CH:18]=[CH:17][CH:16]=1)[O:12][CH:5]1[C:4]2[C:9](=[N:10][CH:11]=[C:2]([C:28]3[CH:33]=[CH:32][CH:31]=[C:30]([N:34]4[CH2:35][CH2:36][O:37][CH2:38][CH2:39]4)[CH:29]=3)[CH:3]=2)[NH:8][CH2:7][CH2:6]1

Komponenten

4

Edukt 2

HCID 41926634-(3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)morpholineHCID 578858956-Bromo-4-(3-chlorophenoxy)-1,2,3,4-tetrahydro-[1,8]naphthyridine

Produkt 1

HCID 578859534-(3-Chlorophenoxy)-6-(3-morpholin-4-yl-phenyl)-1,2,3,4-tetrahydro-[1,8]naphthyridineAusbeute 49 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21226206Ethyl acetate hexaneLösungsmittel

Versuchsvorschrift

6-Bromo-4-(3-chlorophenoxy)-1,2,3,4-tetrahydro-[1,8]naphthyridine (20 mg) was reacted with 4-[3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl]morpholine (23.9 mg) as in General Procedure 13. Silica gel chromatography using a gradient of 0-100% ethyl acetate/hexane as the eluting solvent gave the title compound as a yellow foam (49% yield). LCMS: m/z=422.18 (M+H+), 1H-NMR (CDCl3, 400 MHz) δ 2.00-2.11 (m, 1H), 2.22-2.26 (m, 1H), 3.19 (t, J=4.8 Hz, 4H), 3.40-3.45 (m, 1H), 3.58-3.64 (m, 1H), 3.88 (t, J=4.8 Hz, 4H), 5.14 (bs, 1H), 5.37 (t, J=1.0 Hz, 1H), 6.82-6.92 (m, 2H), 6.92 (s, 1H), 6.95-7.02 (m, 2H), 7.03-7.08 (m, 1H), 7.20-7.33 (m, 2H), 7.55 (d, J=1.9 Hz, 1H), 8.27 (d, J=2.1 Hz, 1H).

Quellen und Nachweise

ORD-Eintrag
ord-385ef0b9ad6f4e4ab8bcd763b757cb88
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08080561B2

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